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2+ Week Northern Italy Grand Tour
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Sandee Hughes
New Orleans, LA Travel Agent
Sandee Hughes
New Orleans, LA Travel Agent· 9 Years of Experience
BucketList Travel Advisors, an independent agent with Nexion, LLC, a Travel Leaders Network Affiliate Agency
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Our trip to Madrid and Barcelona in June 2025 was truly a trip of a lifetime. Sandee took the time to understand that we wanted a... Read More >
COUNTRIES VISITED:Italy
PLACES VISITED:Chianti, Cinque Terre, Cortona, Florence, Lake Como, Milan, Pisa, Portofino, Rome, San Gimignano, Siena, Tuscany, Vatican City, Veneto, Venice
SUGGESTED DURATION:18 Days
I am excited to provide you with a two and half week itinerary of Northern Italy from Rome to Milan.
This package itinerary was designed to provide all the highlights of Northern Italy with time in the key cities including a week in Tuscany with a private driver.
Included in the itinerary are centrally located boutique hotels. Private transfers with drivers and stops in must-see cities along the way.
Private tours are included in the most important cities and villages throughout your time in Italy including required tickets and entrance fees, a cooking class in Tuscany, and private boat tours on Lake Como.
Enjoy a taste of Italy!
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DAY1
Rome
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Ancient Rome Explorations
Your private English-speaking driver will arrive at your hotel to pick you up from the lobby of the hotel and escort you to the Colosseum to meet your private guide for a 4-hour tour of the Colosseum, and Forum.
Start your day touring some of Rome's most iconic ancient sites. Your English-speaking guide will lead you around Palatine Hill. One of the oldest locations in Rome it is considered the origin of the Roman Empire.
From here, you will explore the most ancient sites including the Coliseum and the Forum understanding the culture and the events that occurred there and their importance to the ancient Roman culture.
Spend the remainder of your day exploring Rome on your own, walking the streets surrounding the ancient regions of Rome. Explore the aqueducts, and visit the Trevi fountain, and the Villa Medici.
Entrance fees are included in your tour.
HIGHLIGHTS:
The Houses of Livia and Augustus are the former Villa of Rome's first emperor.
DAY2
Vatican City
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Vatican City visit
Your private English-speaking driver will arrive at your hotel to pick you up from the front door of your accommodations and escort you to the Vatican for a four-hour private guided tour.
Vatican City is the most popular tourist destination in Rome. You will see all the highlights of this vast religious complex. From walking through Michelangelo's Sistine Chapel to the halls filled with some of the world's largest collections of art.
St. Peter's Basilica which was first designed by Donato Bramante will astound you as you learn the history of one of the largest and holiest churches in the world.
Finish your visit with time within the Museums of the Vatican viewing some of the world's most famous masterpieces of Renaissance Art.
Entrance fees are included with access to Vatican Museum and Sistine Chapel. Once you leave the Sistine Chapel, your guide will lead you on a walk for 1 km to queue to visit the St Peter Basilica.
HIGHLIGHTS:
Renaissance frescoes in the Raphael Rooms
DAY3
Rome
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Free day in Rome
Today Rome is your oyster.
The vibrant capital of Italy is a unique fusion of rich history, culture, natural beauty, and monuments. It goes much further than the usual tourist sites: delve into Rome's hidden gems that are just a few steps away from the well-trodden paths and monuments.
Here's a short list of Rome's tucked-away treasures that will leave you taken with the city's seemingly endless offerings.
Walk past the famous Pantheon and the elegant and popular Piazza Navona square, the Baroque San Luigi dei Francesi church where you can pop in to view the Caravaggio paintings in its chapel, or visit the Basilica di Sant’Agostino a sacred site filled with Italian artworks.
HIGHLIGHTS:
Throw a coin into the Trevi Fountain
Climb the Spanish Steps
Explore Villa Medici
Shop along the Via Dei Condotti
DAY4
Tuscany
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Rome to Tuscany
You will meet your driver in the hotel lobby to transfer you and your luggage to your accommodations in Tuscany.
About an hour's drive south of Montepulciano, you will travel through the famed Val d’Orcia, a distinctive rural agricultural landscape that still reflects its Renaissance character and aesthetic.
You will pass through a landscape covered with settlements some dating back thousands of years. This area was important during the Etruscan period and developed during the era of the Roman Empire.
Your next stop will be the beautiful town of Montepulciano. You will have two hours to visit a few wineries located within the hilltop town to explore one of the local wine bars and sample many of the famed Brunello (Sangiovese) wines of this southern Tuscany region.
HIGHLIGHTS:
The 14th Century Palazzo Comunale
Torre di Pulcinella clock tower
DAY5
Siena
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At the heart of Tuscany in Siena
Your private driver will arrive to take you on a scenic drive to the beautiful town of Siena.
Once one of the most important cities in the region in the Middle Ages. A UNESCO World Heritage site, it is still well preserved and a key region in understanding Tuscany's importance.
Your driver will connect you with your English-speaking guide for a tour of this historic city.
From viewing the medieval brick buildings that surround you. The fan-shaped central square, Piazza del Campo, is the site of the Palazzo Pubblico, the Gothic town hall, and Torre del Mangia, a slender 14th-century tower with sweeping views from its distinctive white crown. The city’s 17 historic “contra de” (districts) extend outward from the piazza.
Your walking tour will explain the history and significance of this medieval city.
HIGHLIGHTS:
Siena Cathedral
DAY6
San Gimignano
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Wine tasting in San Gimignano
Your private driver will arrive to take you on an approximately one-hour scenic drive each way to the beautiful town of San Gimignano.
A UNESCO World Heritage location, the "Town of Fine Towers" is best known for its architecture.
Explore all the highlights of the area, its medieval architecture, and dozens of its tower houses, which, along with its hilltop setting and encircling walls, form "an unforgettable skyline".
Once you complete your visit to the town. In the last 30 years, the town has developed a quality policy in the world of wine. The wines produced in the area of San Gimignano are some of the only white you will find in the region: Vernaccia di San Gimignano DOCG, San Gimignano.
On the ground floor of La Rocca, you can enjoy wine tasting: sixteen different labels of Vernaccia di San Gimignano DOCG and Vernaccia di San Gimignano DOCG Riserva famed white wines of Tuscany.
HIGHLIGHTS:
Frescoes of the Duomo di San Gimignano
DAY7
Pisa
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Head to Tuscany's coastal region
Starting in Pisa, visit the Piazza dei Miracoli, to view the Duomo complex, and climb to the top of the Leaning Tower of Pisa.
Step inside the Duomo to see the beautifully designed pulpit, designed by Giovanni Pisano in the early 14th century. Rumor is the amphora to the right of the apse was used by Jesus for turning water into wine.
After exploring the intricate complexities of the Duomo, walk over to the Piazza del Cavalieri (Knights’ Square), to admire the architecture and grab a bite at a local cafe.
After Pisa, you will hop back in the car for a short drive to the historic center of Lucca.
Lucca is historic and charming. It is known for the walls that make a ring around the city. With many historical sites and one of the best-preserved towns in Tuscany, it is a must-see stop on any Tuscan itinerary
HIGHLIGHTS:
The leaning tower of Pisa
Medieval Agostini Palace
Casa di Puccini home in Lucca
DAY8
Chianti
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Countryside cooking class
This full-day tour will have you cooking in a spacious Tuscan kitchen. It is one of the best experiences guests rave about.
The secret to Tuscan cuisine is simplicity. Farmers sought flavor & nourishment from whatever ingredients were most readily at hand, which became recipes, which then got passed down from generation to generation.
For Italians today, one perfect bite magically transports you back to nonna’s kitchen, where you will pass the afternoon stirring, cutting & rolling just as they did in the old country.
Your personal chef will be waiting for you at the farmhouse immersed in vineyards and olive trees all around. You will be introduced to the most antique and traditional Tuscan recipes and will and next will start kneading with you!
You will learn some of our cuisine’s secrets…one of the best souvenirs you can bring home with you!
After the cooking lesson, you will enjoy the cooked meal accompanied by excellent local wines.
HIGHLIGHTS:
Sample some of the most famous Tuscan specialties
DAY9
Cortona
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Exploring scenic eastern Tuscany
Your private driver will arrive to take you on an approximately one-hour scenic drive southeast to the beautiful town of Arezzo and then on to Cortona.
Today’s itinerary begins in the setting of the movie Life is Beautiful.
This hilled town of Arezzo will offer you a bit of a hike as you climb from the bottom of the hill and work your way up to the many Piazza and Cathedrals and beyond to the highest points of the town where you will find the Cathedral of Santi Donato e Pietro, and Arezzo’s Duomo, and the Medici Fortress for a full history of the power and politics of the region.
You may recognize the location if you have seen the film "Under the Tuscan Sun"
Cortona is considered one of the most beautiful medieval small towns with cobblestoned streets and beautiful views of the Tuscan countryside. As you explore inside and outside the city walls, you can spend hours strolling the streets visiting many Piazza and religious sites, or stopping for lunch.
HIGHLIGHTS:
Roman amphitheater of Arezzo
Etruscan and Roman archeological museum.
The Diocesan Museum in Cortona
DAY10
Florence
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Into the heart of Tuscany
Your driver will arrive early to take you into the beautiful city of Florence.
Once you arrive at Firenze, after checking into your Florence hotel, you will meet your English-speaking local private guide for a 3-hour walking tour through Florence.
The flowering of Florence in art, culture, and international trade began in the 13th century and it reached its peak in the 15th century under the reign of the Medici family, who ruled over the city for more than three centuries.
Everywhere you turn in Florence, you find extraordinary works of art and architecture, from the Palazzo Vecchio to the world-famous Uffizi Gallery to the Cathedral with its magnificent dome and the tower designed by Giotto. Along the river Arno, the Ponte Vecchio with its jewelry shops is a must for all those who pass through the city, as well as the splendid Boboli gardens across the river.
HIGHLIGHTS:
Michelangelo statue at the Accademia Gallery.
Uffizi Gallery exhibition of Botticelli’s “The Birth of Venus”
Piazzale Michelangelo
DAY11
Florence
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Veneto
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The best of Italy - Florence & Venice
Some not to be missed sites can be found by crossing the Ponte Santa Trinita to Oltrarno on the other side of the Arno to the Piazza Santo Spirito. Surrounding the square are artisan workshops from bookbinders to sculptors, and make for unique browsing.
Find great shopping here including the not to be missed Florence Leather Market.
Your private driver will arrive to pick you and your luggage up from your hotel to escort you to Venice.
Upon arriving into the Venice region, your driver will connect you with your private water taxi driver to transfer you to your Venetian hotel
After you are settled you will enjoy a classic gondola ride through Venice and explore the waterways around Venice by one of the city's most traditional and unique transportation methods.
Sit back and enjoy as an expert gondolier navigating hidden passages and the Grand Canal. Enjoy the peace and tranquility of being on the water and seeing Venice from a whole new perspective
HIGHLIGHTS:
Santa Maria Novella in Florence
St. Marks Square at Sunset
DAY12
Venice
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Venice Classic Tour
This is an introductory sightseeing tour of Venice visiting St. Mark’ s Square, the Basilica and the Doge’ s Palace. St. Mark's square was the political and religious centre of the Republic of Venice;
Since ancient times it has been a place extraordinarily rich in historical and artistic value.
A tour of the sumptuous halls of power in the Doge’s Palace, once the seat of the Serenissima government, offers an insight of Venice's efficient and fascinating political life.
Admire the paintings extolling the Myth of Venice, its conquests and diplomatic successes.
Relive the pomp and ceremony of one of Europe’s most prestigious capitals.
The Basilica of Saint Mark, now the city’s cathedral, was once both the Ducal Chapel and a reflection of State magnificence. You’ll be dazzled by its golden mosaics and precious marbles, works of art that have turned the church into one of the most beautiful monuments in the world.
HIGHLIGHTS:
Explore the maze-like little neighborhoods and discover some of the most interesting areas
DAY13
Venice
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Cinque Terre
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Onto the Italian Riviera
A private boat will arrive at your hotel to connect you and your luggage with a car and driver to take you on to the Italian Riviera.
You arrive at the largest of the five villages, Monterosso. Featuring both historical medieval sites and the beach, you will enjoy the best of both worlds.
Enjoy exploring the town and indulging in open-air cafes and fresh coastal breezes as you relax and enjoy your evening.
HIGHLIGHTS:
Church of San Giovanni Battista,
DAY14
Cinque Terre
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Hiking the Cinque Terre
You will meet your half-day English-speaking guide who will take you on a pleasant hike through the beautiful region of Cinque Terre from Monterosso.
A daily Cinque Terre card, gives you access to the hiking trails together with unlimited train travel on the Cinque Terre Express trains on the Levanto - Cinque Terre - La Spezia line.
Visit the villages of Cinque Terre.
Starting from Monterosso you will follow the footpaths with breathtaking views winding along Mediterranean groves and partly deserted fields and vineyards.
After your tour you can choose if you want to keep exploring or return to Monterosso for some beach relaxation time.
HIGHLIGHTS:
Soviore Sanctuary which dates back to the XVII Century
DAY15
Portofino
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Milan
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From the coast to the capital
After breakfast at the hotel, you will get ready to reach Milan.
Portofino is a cosmopolitan holiday resort wrapped up in an aura of nostalgia for the 60s, the years during which the village started shaping into the luxury travel destination it is now. It managed to maintain the original allure of a fishing village that is abundant in local customs and traditions. It is known for its amazingly beautiful harbor and clean water.
La Piazzetta (Portofino's main square) is adjacent to the port and buzzes with life and people, filled as it is with yachts and upmarket restaurants. The alleys around the port feature boutiques and eateries, creating a district of quaint buildings interspersed with art galleries.
You will have time to enjoy lunch. Portofino is renowned for bringing in many different kinds of seafood, from white fishes that dominate many of their meals to squid and octopi, to shellfish like shrimp.
HIGHLIGHTS:
Portofino Lighthouse
DAY16
Milan
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A walking tour of Milan
You will meet your guide for your private walking tour introducing you to Italy’s most stylish city.
Stop by the alluring Galleria Vittorio Emanuele II shopping gallery, a 19th-century glass vaulted shopping arcade.
Brimming with fashionable shops and cafes, it is often called the ‘salotto di Milano’ or ‘Milan’s drawing room’ for its importance over the years as a common meeting point for the people of Milan.
Admire the medieval Sforza Castle.
Next, tour the splendid Duomo, one of the world’s largest, most striking Gothic cathedrals.
Admire Milan’s most famous Opera House, the fabulous La Scala Theatre.
Finally, you will reach a highlight of a visit to Milan at the former Dominican convent of Santa Maria delle Grazie.
It is here that your guide will share information about the convent that houses the famous DaVinci Last Supper painting before leaving you to explore on your own.
HIGHLIGHTS:
Sforzesco Castle
DAY17
Lake Como
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Scenic Drive from Milan to Lake Como
Your private driver will meet you in the lobby of your hotel for the journey from Milan to Lake Como famous for the natural beauty of its setting, handsome villas, and lakeshore resorts found along its shores.
The best way to really see Lake Como is from the lake, aboard a private boat. Your private water taxi offers both indoor and outdoor seating and includes a captain and fuel. All cruises are private, boats will be only for you and your party
Along the water route, your captain will stop in front of all the most famous villas and villages to share their stories.
Visit the Balbianello terraced gardens, a “must” while in Lake Como; thanks to its strategic position at the end of a promontory where the view is unparalleled and breathtaking.
In the old village, along the characteristic stairs, you will find many elegant shops and artisans’ ateliers.
At the end of your cruise, you will be brought back to your departing pier.
HIGHLIGHTS:
Bellagio the "pearl of the lake"
DAY18
Milan
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A final day in Italy
Enjoy the day to explore Milan on your own:
Milan is the second largest city in Italy. Almost everything in Milan revolves around the fashion industry. Most famous designers and fashion houses tend to be located in the city — the area around Via Monte Napoleone and Via Della Spiga is the heart and home to many fashion industry flagship stores.
Navigli, by the canals, is another exciting neighborhood famous for its nightlife, while Brera is an artsy enclave.
Finish your visit with some of fantastic Milanese gastronomy at one of the rooftop restaurants with Duomo views.
HIGHLIGHTS:
Galleria Vittorio Emanuele II
FINAL THOUGHTS
As this is fully customized, you can be the designer of your own Italian journey.
I look forward to assisting you with designing an amazing Italian itinerary.